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

HRID 451768

반응식

HRID 451768 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0db4cce6a1e04c7090574e707c3d1e2a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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