Diisopropylethylamine → HCID 70177531, compound

HRID 2185562Notes

Reaction equation

HRID 2185562 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@H:14]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:16])[CH2:4]1)=O.FC(F)(F)C(O)=O.[O:40]=[C:41]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:42][CH2:43][CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCOC(C)=O>[O:40]=[C:41]([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[CH2:42][CH2:43][CH:44]1[CH2:45][CH2:46][N:47]([CH2:1][C@@H:3]2[C@@H:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:6][N:5]([C@H:14]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[O:16])[CH2:4]2)[CH2:48][CH2:49]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22458282HCID 22458282, compoundHCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 70177531HCID 70177531, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Molecular sieve pellets (3 Å) were added to a solution of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, 4-(methoxy)benzyl ester (30 mg, 0.069 mmol, Aldehyde 5), 4-(3-oxo-3-phenylpropyl)piperidine trifluoroacetate (25 mg. 0.075 mmol, from Step D), and DIEA (0.013 mL, 10 mg, 0.075 mmol) in 1,2-dichloroethane (0.70 mL). The mixture was stirred for 15 min at rt before the addition of sodium triacetoxyborohydride (17 mg, 0.080 mmol). After 2.5 h, the mixture was diluted with EtOAc (20 mL) and washed with sat'd NaHCO3 (10 mL) followed by sat'd NaCl (10 mL). The organic layer was dried (Na2SO4), decanted, and evaporated. Purification by flash column chromatography on silica gel, eluting with 15-20% EtOAc/0.5% CH3OH/CH2Cl2 gave 30 mg of the title compound as a colorless viscous oil. ESI-MS: 637 (M+H).

Workup

  1. washwashed with sat'd NaHCO3 (10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customdecanted
  4. customevaporated
  5. customPurification by flash column chromatography on silica gel
  6. washeluting with 15-20% EtOAc/0.5% CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-0e104e10602441c0b558294a0152b61c
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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