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

HRID 451768

反応式

HRID 451768 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0db4cce6a1e04c7090574e707c3d1e2a
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

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