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Triethylamine → (1S,2S)-2-amino-1-((R)-1-benzhydrylpiperidin-2-yl)-3-(3,5-difluorophenyl)propan-1-ol

HRID 132937
Notes
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Reaction equation

HRID 132937 reaction equation
C(O[C@H:5]1[CH2:9][N:8](C(OC(C)(C)C)=O)[C@@H:7]([CH2:17]O)[CH2:6]1)C=C.F[C:20]1[CH:21]=[C:22]([CH:55]=[C:56](F)[CH:57]=1)[CH2:23][C@H:24](C(N1[C@@H](CC2C=CC=CC=2)COC1=O)=O)[C@@H:25]([CH:27]1[CH2:32][CH2:31][CH2:30]CN1C(OC(C)(C)C)=O)O.C([C@H]1COC(=O)N1[C:72](=[O:83])[CH2:73][CH2:74][C:75]1[CH:80]=[C:79]([F:81])[CH:78]=[C:77]([F:82])[CH:76]=1)C1C=CC=CC=1.B(OS(C(F)(F)F)(=O)=O)(CCCC)CCCC.C([N:103](CC)CC)C.C(O[C@H]1CN(C(OC(C)(C)C)=O)[C@@H](C(O)=O)C1)C=C>C(Cl)Cl.CO>[NH2:103][C@@H:73]([CH2:74][C:75]1[CH:76]=[C:77]([F:82])[CH:78]=[C:79]([F:81])[CH:80]=1)[C@@H:72]([C@H:9]1[CH2:5][CH2:6][CH2:17][CH2:7][N:8]1[CH:23]([C:22]1[CH:21]=[CH:20][CH:57]=[CH:56][CH:55]=1)[C:24]1[CH:25]=[CH:27][CH:32]=[CH:31][CH:30]=1)[OH:83]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 2724243Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dibutylborinic acidHCID 59733915(S)-4-benzyl-3-(3-(3,5-difluorophenyl)propanoyl)oxazolidin-2-oneHCID 67315699(4R)-1-Boc-4-(2-propen-1-yloxy)-D-prolineHCID 67315914(2R,4R)-tert-butyl 4-(allyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
HCID 69196027
tert-butyl 2-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)piperidine-1-carboxylate

Product 1

HCID 58608199(1S,2S)-2-amino-1-((R)-1-benzhydrylpiperidin-2-yl)-3-(3,5-difluorophenyl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Step I (3): Preparation of tert-butyl 2-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)piperidine-1-carboxylate. To a solution of (S)-4-benzyl-3-(3-(3,5-difluorophenyl)propanoyl)oxazolidin-2-one (Preparation M, 2.2 g, 6.57 mmol) in CH2Cl2 (100 mL) at −78° C. was added Bu2BOTf (di-n-butylboron triflate) (7.9 ml, 7.9 mmol, 1M in CH2Cl2) and triethyl amine (1.4 mL, 10 mmol). The resulting mixture was brought up to 0° C. and stirred for 20 min. The mixture was cooled back to −78° C. and a solution of tert-butyl 2-formylpiperidine-1-carboxylate (Step I (2), 1.4 g, 6.57 mmol) in CH2Cl2 (100 mL) was added. When the addition was complete, the mixture was allowed to warm to and stirred at rt overnight. MeOH was added and the mixture was concentrated in vacuo. The crude mixture was purified by silica gel Flash chromatography to give 2.0 g of the title compound: 1H NMR (CDCl3, 500 MHz) δ 1.42-1.66 (14H, m), 1.86-2.26 (1H, m), 2.62-3.40 (6H, m), 3.84-4.69 (7H, m), 6.58-6.65 (1H, m), 6.81-6.85 (2H, m), 6.90-6.96 (2H, m), 7.22-7.27 (3H, m). MS (ESI) (M+Na)+ 581.12.

Workup

  1. customwas brought up to 0° C.
  2. additionWhen the addition
  3. temperatureto warm to and
  4. stirringstirred at rt overnight
  5. concentrationthe mixture was concentrated in vacuo
  6. customThe crude mixture was purified by silica gel Flash chromatography

Sources & evidence

ORD record
ord-f515ed98c4e14f248530b3e0e0c654c8
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07388007B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes