Ethanol → 1,1-Dimethylethyl N-[(1S,3R)-4-hydroxy-1-(hydroxymethyl)-3-methylbutyl]carbamate

HRID 1499486Notes

Reaction equation

HRID 1499486 reaction equation
[CH3:1][C@H:2]1[C:6](=[O:7])[N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:4]([C:15](OC)=[O:16])[CH2:3]1.[BH4-].[Na+].CCO>C1COCC1.CCOC(C)=O>[OH:7][CH2:6][C@H:2]([CH3:1])[CH2:3][C@H:4]([NH:5][C:8](=[O:9])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:15][OH:16]

Participants

6

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 10934126Methyl (2S,4R)-1-(tert-butoxycarbonyl)-4-methylpyroglutamate

Product 1

HCID 247535131,1-Dimethylethyl N-[(1S,3R)-4-hydroxy-1-(hydroxymethyl)-3-methylbutyl]carbamate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 1-tert-butyl 2-methyl (2S,4R)-4-methyl-5-oxopyrrolidine-1,2-dicarboxylate (0.47 g, 1.8 mmol) in THF (4.0 mL) at −10° C., NaBH4 (0.207 g, 5.48 mmol) was added followed by EtOH (1.0 mL). After stirring at −10° C. for 1 h, the mixture was allowed to warm to room temperature and stirred for 15 h. The reaction mixture was then diluted with EtOAc (50 mL), washed with water (25 mL) and brine (30 mL), then dried over Na2SO4 and concentrated under reduced pressure. The resulting crude product (0.39 g, 92%) was used directly in the next step without further purification. LCMS calc. for C11H24NO4 (M+H)+: m/z=234.2. found no ionization.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 15 h
  3. washwashed with water (25 mL) and brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product (0.39 g, 92%) was used directly in the next step without further purification

Sources & evidence

ORD record
ord-97fe427d78684206ace0e953064d7b8b
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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