(5R)-3-(4-(1-Benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluorophenyl)-5-azidomethyl-oxazolidin-2-one → (5S)-5-(Aminomethyl)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3-fluorophenyl]oxazolidin-2-one

HRID 1452608Notes

Reaction equation

HRID 1452608 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13](F)[C:12]([C:16]3[CH2:17][CH2:18][N:19]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:20][CH:21]=3)=[C:11]([F:29])[CH:10]=2)[CH2:4]1.N(C[C@@H]1OC(=O)N(C2C=CC(C3CCN(CC4C=CC=CC=4)CC=3)=C(F)C=2)C1)=[N+]=[N-]>>[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([C:16]3[CH2:17][CH2:18][N:19]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:20][CH:21]=3)=[C:11]([F:29])[CH:10]=2)[CH2:4]1

Participants

3

Reactant 2

HCID 11524312(5R)-3-(4-(1-Benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluorophenyl)-5-azidomethyl-oxazolidin-2-oneHCID 57526982(5S)-5-(Aminomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]oxazolidin-2-one

Product 1

HCID 11574477(5S)-5-(Aminomethyl)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3-fluorophenyl]oxazolidin-2-one

Procedure

The procedure was identical to that used for Intermediate 54, except (5R)-5-(azidomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3-fluorophenyl]-1,3-oxazolidin-2-one (WO 0181350 A1) (21.19 g, 52.00 mmol) was used as starting material. 13 g of the title product was obtained.

Sources & evidence

ORD record
ord-8fdabe0faf9b4079b9e458126ad8ca1b
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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