Potassium sodium tartarate → (2S,4R)-[4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-methanol

HRID 458367ノート

反応式

HRID 458367 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:14][C:15]([C@@H:17]1[CH2:21][C@@H:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:19][N:18]1[S:27]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)(=[O:29])=[O:28])=O)C1C=CC=CC=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC>[C:23]([O:22][C@H:20]1[CH2:19][N:18]([S:27]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)(=[O:29])=[O:28])[C@H:17]([CH2:15][OH:14])[CH2:21]1)([CH3:26])([CH3:25])[CH3:24]

参加物

5

反応物 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride2 回HCID 69433308(2S,4R)-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl ester

生成物 1

HCID 69429584(2S,4R)-[4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-methanol収率 87.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

LAH reduction: To a slurry of lithium aluminium hydride (0.72 g) in Et2O (120 ml) was added a solution of (2S,4R)-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl ester (9.0 g) in Et2O (80 ml) dropwise at −15° C. within 0.5 h. The suspension was stirred for 2 h at the same temperature, then a saturated solution of potassium-sodium tartrate (10 ml) was added dropwise. The slurry was filtered through a pad of filter aid and was washed with Et2O. The combined filtrates were washed with brine, dried over magnesium sulphate and concentrated. The residue was crystallized from acetone/Et2O/hexane to obtain (2S,4R)-[4-tert-butoxy-1-(naphthalene-2-sulfonyl) -pyrrolidin-2-yl]-methanol (6.1 g) as a colorless solid, mp 124–125° C.; MS 363 (M).

後処理

  1. filtrationThe slurry was filtered through a pad of filter aid
  2. washwas washed with Et2O
  3. washThe combined filtrates were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was crystallized from acetone/Et2O/hexane

出典と根拠

ORDレコード
ord-79b67884255542d2a3b21537fcbb32f7
出典データセット
uspto-grants-2007_03
特許番号
US07189756B2

反応ノート

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