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

HRID 1747144ノート

反応式

HRID 1747144 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-fae468aeb8654c4582e1ed5ef3cb6643
出典データセット
uspto-grants-2015_10
特許番号
US09150532B2

反応ノート

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