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

HRID 458367노트

반응식

HRID 458367 반응식
[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]

참가 물질

5

반응물 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride2회HCID 69433308(2S,4R)-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl ester

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-79b67884255542d2a3b21537fcbb32f7
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189756B2

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