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Tetrahydrofuran → HCID 58631212, compound

HRID 1520542
Notes
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Reaction equation

HRID 1520542 reaction equation
C1COCC1.[C:6]([O:10][C:11]([N:13]1[C@H:17]([CH2:18][F:19])[C@@H:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[O:30][N:29]=[C:28]([C:31](OCC)=[O:32])[CH:27]=3)=[CH:22][CH:21]=2)[O:15][C:14]1([CH3:37])[CH3:36])=[O:12])([CH3:9])([CH3:8])[CH3:7].[BH4-].[Na+]>CO>[F:19][CH2:18][C@@H:17]1[C@@H:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[O:30][N:29]=[C:28]([CH2:31][OH:32])[CH:27]=3)=[CH:22][CH:21]=2)[O:15][C:14]([CH3:37])([CH3:36])[N:13]1[C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 58631154HCID 58631154, compound

Product 1

HCID 58631212HCID 58631212, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) THF (25 ml) solution of ethyl 5-(4-((4S,5R)-3-(tert-butoxycarbonyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-5-yl)phenyl)isoxazole-3-carboxylate (1.0 g, 2.2 mmol) is added sodium borohydride (0.25 g, 6.7 mmol) followed by methanol (3 ml added slowly). The reaction is stirred for 30 minutes at 0° C. and for one hour at room temperature. The excess sodium borohydride is quenched by the addition of saturated aqueous ammonium chloride (5 ml). The reaction mixture is diluted with ethyl acetate (50 ml) and water (25 ml). The layers were mixed and allowed to separate. The organic phase is collected, dried over sodium sulfate and concentrated to give the product, (4S,5R)-tert-butyl 4-(fluoromethyl)-5-(4-(3-(hydroxymethyl)isoxazol-5-yl)phenyl)-2,2-dimethyl-oxazolidine-3-carboxylate (875 mg, 96%), as a viscous oil. 1H NMR (400 MHz, CDCl3) 1.52 (s, 9H) 1.59 (s, 3H) 1.74 (br. s., 3H) 2.03-2.08 (m, 1H) 3.83-3.96 (m, 1H) 4.40-4.60 (m, 2H) 4.85 (d, J=6.06 Hz, 2H) 5.19 (d, J=7.58 Hz, 1H) 6.63 (s, 1H) 7.57 (d, J=8.34 Hz, 2H) 7.82 (d, J=8.34 Hz, 2H); m/z (Cl) 407 ([M+H]+.

Workup

  1. additionadded slowly)
  2. customThe excess sodium borohydride is quenched by the addition of saturated aqueous ammonium chloride (5 ml)
  3. additionThe reaction mixture is diluted with ethyl acetate (50 ml) and water (25 ml)
  4. additionThe layers were mixed
  5. customto separate
  6. customThe organic phase is collected
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a29bcfbe33014491aaea60b911626193
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073894B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes