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

HRID 731539

Reaction equation

HRID 731539 reaction equation
[C:1]([NH:11][C@@H:12]1[CH2:17][O:16][C:14](=[O:15])[CH2:13]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:18][NH:19][CH3:20]>C1COCC1>[CH3:18][N:19]([CH3:20])[C:14](=[O:15])[CH2:13][C@@H:12]([NH:11][C:1](=[O:2])[O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:17][OH:16]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 697922Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamate

Product 1

HCID 59186705N-[(1R)-3-(Dimethylamino)-1-(hydroxymethyl)-3-oxopropyl]carbamic acid phenylmethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(S)-((carbobenzyloxy)amino)-γ-butyrolactone (prepared according to the procedure described in McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952, 7.72 g, 32.8 mmol) in THF (100 mL) was saturated with gaseous dimethylamine, stirred at room temperature for 16 hours, and concentrated. The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes to give the desired product (9.16 g, 99%). MS (CI) m/e 281 (M+H)+.

Workup

  1. concentrationconcentrated
  2. filtrationThe residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes

Sources & evidence

ORD record
ord-2987bbac10384ccc87a86bdbf15acfb7
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Linked notes

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