Water → HCID 67325214, compound

HRID 1465995Notes

Reaction equation

HRID 1465995 reaction equation
[C:1](=[O:19])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[N:5]=[CH:6][S:7][CH:8]=1.[NH:20]1[CH2:24][CH2:23][CH:22]([CH2:25][OH:26])[CH2:21]1.O>ClCCl.CO>[OH:26][CH2:25][CH:22]1[CH2:23][CH2:24][N:20]([C:1]([O:2][CH2:3][C:4]2[N:5]=[CH:6][S:7][CH:8]=2)=[O:19])[CH2:21]1

Participants

6

Reactant 3

HCID 962WaterHCID 13400657(Pyrrolidin-3-yl)methanolHCID 18939632HCID 18939632, compound

Product 1

HCID 67325214HCID 67325214, compoundYield 21.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.00 g (10.70 mmol) of thiazol-4-ylmethyl 4-nitrophenyl carbonate in 20 ml of dichloromethane is added at ambient temperature, via a dropping funnel, to a solution of 1.13 g (11.24 mmol) of pyrrolidin-3-ylmethanol (commercial) in 20 ml of methanol. The solution is stirred for 15 hours. Water is subsequently added to the reaction medium. After extraction of the aqueous phase with dichloromethane, the organic phases are successively washed with a 1M aqueous sodium hydroxide solution and then with a saturated aqueous sodium chloride solution. After having dried the organic phases over sodium sulphate, the mixture is filtered and the filtrate is evaporated to dryness. 0.56 g of the desired product is thus obtained in the form of an oil after purification on a column of silica gel, elution being carried out with a dichloromethane/methanol (97/3 to 95/5) mixture.

Workup

  1. extractionAfter extraction of the aqueous phase with dichloromethane
  2. washthe organic phases are successively washed with a 1M aqueous sodium hydroxide solution
  3. dry with materialAfter having dried the organic phases over sodium sulphate
  4. filtrationthe mixture is filtered
  5. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-db0656c61b7f481c9e63db63a9bfc5c4
Source dataset
uspto-grants-2015_04
Patent number
US09000010B2

Reaction notes

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