Acetic Anhydride → Acetamide, N-[(1R,2S)-2,3-dihydro-2-hydroxy-1H-inden-1-yl]- (9CI)

HRID 1958458Notes

Reaction equation

HRID 1958458 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1[OH:11].[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(Cl)Cl>[OH:11][C@H:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@H:2]1[NH:1][C:12](=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanol

Product 1

HCID 22874977Acetamide, N-[(1R,2S)-2,3-dihydro-2-hydroxy-1H-inden-1-yl]- (9CI)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R,2S)-1-amino-2-indanol (2.0 g, 13.4 mmol) is suspended in 100 mL DCM and at RT it is combined with acetic anhydride (1.27 mL, 13.4 mmol). The reaction mixture is stirred for 1 h at RT, once the reaction is complete the solvent is eliminated using the rotary evaporator and the crude product B-1b (HPLC-MS: tRet.=0.81 min; MS (M+H)+=192) is used in the subsequent reactions without further purification.

Workup

  1. customthe rotary evaporator
  2. customthe crude product B-1b (HPLC-MS: tRet.=0.81 min; MS (M+H)+=192) is used in the subsequent reactions without further purification

Sources & evidence

ORD record
ord-114fe4fbef9c4da6ab257f5a2b9eca38
Source dataset
uspto-grants-2013_04
Patent number
US08410126B2

Reaction notes

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