Hydrochloric Acid → (S)-2-(p-toluenesulfonylamino)-1,4-butanediol

HRID 1646046Notes

Reaction equation

HRID 1646046 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@H:11]([C:17](OC)=[O:18])[CH2:12][C:13](OC)=[O:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[BH4-].[Na+].[Li+].[Cl-].Cl>O1CCCC1>[C:1]1([CH3:21])[CH:2]=[CH:3][C:4]([S:7]([NH:10][C@@H:11]([CH2:12][CH2:13][OH:14])[CH2:17][OH:18])(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 25047715Dimethyl N-(p-toluenesulfonyl)-L-aspartate

Product 1

HCID 10934189(S)-2-(p-toluenesulfonylamino)-1,4-butanediol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dimethyl N-(p-toluenesulfonyl)-L-aspartate, (2.0 g; J. M. Theobald, M. W. Williams, G. T. Young, J. Chem. Soc., 1927 (1963)) was dissolved in tetrahydrofuran (20 mL) and NaBH4 (1.5 g) and LiCl (1.5 g) added and the mixture stirred at 0° C. for 60 to 64 hours. Ten percent hydrochloric acid (10 mL) was slowly added (caution!gas evolution) and the mixture extracted with ethyl acetate (3×20 mL). The combined organic extracts were concentrated and the residue dried under vacuum to give (S)-2-(p-toluene-sulfonylamino)-1,4-butanediol, 2, as an off-white solid (1.95 g; HPLC: 97.7%).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×20 mL)
  2. concentrationThe combined organic extracts were concentrated
  3. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-3dc98a9b5f6e4e0eb086c47c80c0a384
Source dataset
uspto-grants-1993_01
Patent number
US05177217

Reaction notes

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