Lithium borohydride → Tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

HRID 1504838Notes

Reaction equation

HRID 1504838 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14](OC)=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>C1COCC1.[Cl-].[NH4+]>[OH:15][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11][S:12][CH3:13]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 11097398(S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-(methylthio)butanoate

Product 1

HCID 11356792Tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of methyl N-(tert-butoxycarbonyl)methioninate (47.7 g, 0.181 mol) in THF (500 mL) was added lithium borohydride (16.0 g, 0.734 mol) at 0° C. The reaction mixture was allowed to warm to room temperature. After 2 hours, the reaction mixture was diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate. MS ESI calc'd. for C10H22NO3S [M+H]+ 236. found 236. 1H NMR (400 MHz, CD3OD) δ 3.68-3.64 (m, 1H), 3.54-3.47 (m, 2H), 2.59-2.48 (m, 2H), 2.10 (s, 3H), 1.88-1.64 (m, 2H), 1.49 (s, 9H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55297eb4a0e54e548b67bcb026d6c517
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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