Sodium borohydride → tert-butyl ((1S,4S)-4-(2-hydroxyethyl)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate

HRID 1747144노트

반응식

HRID 1747144 반응식
[O:1]=[C:2]1[C@:6]2([CH:10]=[CH:9][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]2)[CH2:5][CH2:4][O:3]1.[BH4-].[Na+]>CO>[OH:3][CH2:4][CH2:5][C@@:6]1([CH2:2][OH:1])[CH2:7][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])[CH:9]=[CH:10]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 86708140tert-Butyl (5S,7S)-1-oxo-2-oxaspiro[4.4]non-8-en-7-ylcarbamate

생성물 1

HCID 86708141tert-butyl ((1S,4S)-4-(2-hydroxyethyl)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of the product of Step E (255.9 g, 1.01 mol) and MeOH (2 L) chilled to 2° C. was added NaBH4 (75 g) over ˜2.5 h. The reaction was quenched by addition of aqueous NH4Cl, concentrated under reduced pressure and the mixture was diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with additional EtOAc. The combined organics were washed with brine, dried (MgSO4) and evaporated to give the product of Step F as a thick oil. 1H NMR (400 MHz, CHLOROFORM-d) d=5.74 (d, J=2.0 Hz, 2H), 4.81-4.92 (m, 1H), 4.67-4.79 (m, 1H), 3.71 (t, J=6.1 Hz, 2H), 3.50 (d, J=11.7 Hz, 2H), 2.14-2.28 (m, 2H), 1.70 (td, J=1.6, 6.2 Hz, 4H), 1.52-1.60 (m, 1H), 1.44 (s, 9H)

후처리

  1. customThe reaction was quenched by addition of aqueous NH4Cl
  2. concentrationconcentrated under reduced pressure
  3. additionthe mixture was diluted with water and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with additional EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

출처 및 근거

ORD 기록
ord-fae468aeb8654c4582e1ed5ef3cb6643
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150532B2

반응 노트

불러오는 중…