Dimethylamine → N-[(1R)-3-(Dimethylamino)-1-(hydroxymethyl)-3-oxopropyl]carbamic acid phenylmethyl ester

HRID 1476267Notes

Reaction equation

HRID 1476267 reaction equation
[O:1]=[C:2]1[O:6][CH2:5][C@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[CH3:18][NH:19][CH3:20]>C1COCC1>[CH3:18][N:19]([CH3:20])[C:2](=[O:1])[CH2:3][C@@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 697924(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate2×

Product 1

HCID 59186705N-[(1R)-3-(Dimethylamino)-1-(hydroxymethyl)-3-oxopropyl]carbamic acid phenylmethyl esterYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-benzyl-5-oxotetrahydrofuran-3-ylcarbamate (INTERMEDIATE 3, 18.4 g, 7.8 mmol) in THF (100 ml) was purged, at room temperature, with gaseous dimethylamine for 5 minutes. After stirring at room temp for 14 hours, the reaction mixture was concentrated to dryness, and purified by column chromatography (silica gel, eluting first with 50% ethyl acetate/hexanes followed by 100% acetone) to give the title product (20 g, yield: 91.5%).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. custompurified by column chromatography (silica gel, eluting first with 50% ethyl acetate/hexanes followed by 100% acetone)

Sources & evidence

ORD record
ord-7a8fd0679c8047f0be5c37b56c81588d
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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