Acetic Acid → 3-(Pyrrolidine-1-sulfonyl)propan-1-amine

HRID 1371392Notes

Reaction equation

HRID 1371392 reaction equation
[N:1]1([S:6]([CH2:9][CH2:10][CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].C(O)(=O)C>C(O)(C)C.O.CO>[N:1]1([S:6]([CH2:9][CH2:10][CH2:11][NH2:12])(=[O:7])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 230892282-[3-(pyrrolidin-1-ylsulfonyl)propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 133434513-(Pyrrolidine-1-sulfonyl)propan-1-amineYield 32.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of Intermediate 27 (0.139 g) in isopropanol (7.6 ml) and water (1.3 ml) was treated with sodium borohydride (0.081 g), and the mixture was stirred at room temperature under nitrogen for 19 h. Glacial acetic acid (0.45 ml) was added cautiously and the mixture heated at 80° C. for 2 h. The solvents were evaporated in vacuo to give a white solid, which was dissolved in methanol and applied to a sulphonic acid ion exchange cartridge (10 g Isolute SCX). Elution with methanol followed by 10% 0.880 ammonia in methanol, and evaporation of the ammonia/methanol fraction gave the title compound as a white solid (0.027 g).

Workup

  1. temperaturethe mixture heated at 80° C. for 2 h
  2. customThe solvents were evaporated in vacuo
  3. customto give a white solid, which
  4. washElution with methanol
  5. customfollowed by 10% 0.880 ammonia in methanol, and evaporation of the ammonia/methanol fraction

Sources & evidence

ORD record
ord-d83d1de77f0042618b25a3213cabc5a7
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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