Ammonium Chloride → (S)-tert-butyl 1-cyclohexyl-3-hydroxypentan-2-ylcarbamate

HRID 451768Notes

Reaction equation

HRID 451768 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:9](=[O:12])[CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1.CO>[CH:1]1([CH2:7][C@H:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]([OH:12])[CH2:10][CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 15730499(S)-tert-butyl 1-cyclohexyl-3-oxopentan-2-ylcarbamate

Product 1

HCID 59201568(S)-tert-butyl 1-cyclohexyl-3-hydroxypentan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 1-cyclohexyl-3-oxopentan-2-ylcarbamate in THF/MeOH (604/15 mL) at 0° C. was carefully added NaBH4 (630 mg, 16.66 mmol). After 20 min, sat. aq. NH4Cl was added to quench the reaction, and extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated to give (S)-tert-butyl 1-cyclohexyl-3-hydroxypentan-2-ylcarbamate (4.77 g, 96%, in a ratio of 40:60) as a white solid. MS ESI +ve m/z 286 (M+H).

Workup

  1. customat 0° C.
  2. customto quench
  3. customthe reaction
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0db4cce6a1e04c7090574e707c3d1e2a
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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