Dimethylformamide → Hydroxylamine

HRID 272651Notes

Reaction equation

HRID 272651 reaction equation
[CH:1]1C=NC2[N:7]([OH:10])N=[N:9][C:3]=2[CH:2]=1.Cl.CN(C)CCCN=C=[N:19][CH2:20][CH3:21].CN(C)[CH:25]=[O:26]>>[NH2:7][OH:10].[NH2:9][CH2:3][C@@H:2]([OH:26])[CH3:1].[NH2:19][C@@H:20]([CH3:21])[CH2:25][OH:26]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 3

HCID 787HydroxylamineHCID 80307L-AlaninolHCID 7311736(S)-(+)-1-Aminopropan-2-ol

Procedure

To a solution of J-COOH (e.g., naphthylacetic acid) and HOAt (1 equiv) in dry N,N-dimethylformamide was added 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (1 equiv). After the mixture was stirred at room temperature for one-half hour, a chiral amino alcohol (e.g., (R)- or (S)-1-amino-2-propanol or (R)- or (S)-2-amino-1-propanol, affording a methyl group at R5 or R4, respectively) (1 equiv) was added. The reaction was continued for 16 hours. The reaction mixture was poured into water and extracted by EtOAc twice. The organic layer was washed by 1 N hydrochloric acid twice, 1 N sodium hydroxide twice, brine and dried over sodium sulfate. After evaporation, the product was purified on silica gel column with 10% methanol in methylene chloride.

Sources & evidence

ORD record
ord-374847619c4546649e63133a91d25bba
Source dataset
uspto-grants-2008_11
Patent number
US07456184B2

Reaction notes

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