Stannous chloride dihydrate → [2-Amino-5-(tetrahydro-pyran-2-yloxymethyl)-4-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester

HRID 498224Notes

Reaction equation

HRID 498224 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C:11]([C:22]([F:25])([F:24])[F:23])=[CH:10][C:9]=1[N+:26]([O-])=O)([CH3:4])([CH3:3])[CH3:2].O.O.Cl[Sn]Cl>>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C:11]([C:22]([F:24])([F:25])[F:23])=[CH:10][C:9]=1[NH2:26])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69489653[2-Nitro-5-(tetrahydro-pyran-2-yloxymethyl)-4-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 69487195[2-Amino-5-(tetrahydro-pyran-2-yloxymethyl)-4-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester

Procedure

The title compound was prepared from [2-nitro-5-(tetrahydro-pyran-2-yloxymethyl)-4-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester [prepared from (5-hydroxymethyl-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example A30) (476 mg, 1.42 mmol) by treatment with 3,4-dihydro-2H-pyran (0.19 mL, 2.12 mmol) and p-TsOH (5 mg, 0.03 mmol) in DCM at 0° C., stirring at 0° C. for 15 min and at 23° C. for 18 h.] (0.58 g, 1.38 mmol) reduction with SnCl2.2H2O according to the general procedure J (method b). Obtained as an amorphous yellow substance (414 mg, 77%).

Workup

  1. customObtained as an amorphous yellow substance (414 mg, 77%)

Sources & evidence

ORD record
ord-e687e2be1e0d49018f54e91a66e970f2
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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