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Sodium Bicarbonate → (S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol

HRID 1859004
ノート
印刷プレビュー

反応式

HRID 1859004 の反応式
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[CH2:16][CH2:15][CH2:14][C@@:13]2([CH3:17])[C@H:8]1[CH2:9][CH2:10][CH:11]=[C:12]2[C@H:18]([CH3:21])[CH2:19][OH:20])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+]>C(OC(=O)C)C.[Pd]>[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[CH2:16][CH2:15][CH2:14][C@@:13]2([CH3:17])[C@H:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]2[C@H:18]([CH3:21])[CH2:19][OH:20])([CH3:3])([CH3:4])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 21309369(S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-propan-1-ol

生成物 1

HCID 21309368(S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol収率 95.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

To a solution of 2.27 g (6.7 mMol) of (S)-2-[(4aR,5S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydro-naphtalen-1-yl]-propan-1-ol in 22.7 ml of ethylacetate were added 227 mg of Pd/C 10% and 227 mg of sodium bicarbonate. The reaction mixture was stirred under hydrogen atmosphere overnight, filtered over Speedex using ethylacetate for washing thoroughly and the solvent evaporated in vacuo. The residue was chromatographed over a 250 g Lobar column with hexane/ethylacetate 9/1 to yield 2.18 g (95.5%) of (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphtalen-1-yl]-propan-1-ol as an oily product.

後処理

  1. filtrationfiltered over Speedex
  2. washfor washing thoroughly
  3. customthe solvent evaporated in vacuo
  4. customThe residue was chromatographed over a 250 g Lobar column with hexane/ethylacetate 9/1

出典と根拠

ORDレコード
ord-79098df518bc46bdbc7303e078399e5b
出典データセット
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06153605

反応ノート

読み込み中…

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