(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carboxamide → 2-{(1S)-6-[(diphenylmethylene)amino]-3,4-dihydro-1H-2-benzopyran-1-yl}ethanol

HRID 2056763Notes

Reaction equation

HRID 2056763 reaction equation
[Si]([O:8][CH2:9][CH2:10][C@H:11]1[C:16]2[CH:17]=[CH:18][C:19]([N:21]=[C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:20][C:15]=2[CH2:14][CH2:13][O:12]1)(C(C)(C)C)(C)C.OCC[C@H]1C2C=CC(C(N)=O)=CC=2CCO1>C(O)(=O)C>[C:29]1([C:22](=[N:21][C:19]2[CH:18]=[CH:17][C:16]3[C@H:11]([CH2:10][CH2:9][OH:8])[O:12][CH2:13][CH2:14][C:15]=3[CH:20]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 69308374(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carboxamideHCID 86596018(1S)-1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-N-(diphenylmethylene)-3,4-dihydro-1H-2-benzopyran-6-amine

Product 1

HCID 865960172-{(1S)-6-[(diphenylmethylene)amino]-3,4-dihydro-1H-2-benzopyran-1-yl}ethanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(1S)-1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-N-(diphenylmethylene)-3,4-dihydro-1H-2-benzopyran-6-amine was deprotected with aqueous acetic acid, as described for the preparation of (1S)-1-(2-hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carboxamide, to yield 2-{(1S)-6-[(diphenylmethylene)amino]-3,4-dihydro-1H-2-benzopyran-1-yl}ethanol.

Sources & evidence

ORD record
ord-649d1cf757ae45ee817861f2ff09b875
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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