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

HRID 1006836Notes

Reaction equation

HRID 1006836 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bbc519ad5aa94695a777f7d30aa803a9
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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