Ethanol → tert-butyl [(1R)-2-(3,4-diaminophenoxy)-1-phenylethyl]carbamate

HRID 1038973Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[N+:25]([O-])=O)[O:5][CH2:6][C@H:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[Cl-].[NH4+].C(O)C>[Cl-].[Na+].O.[Fe].C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[NH2:25])[O:5][CH2:6][C@H:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl [(1R)-2-(3-amino-4-nitrophenoxy)-1-phenylethyl]carbamate (Intermediate 5) (346 mg, 0.93 mmol) was placed in a microwave reaction vial (10-20 mL), followed by iron (259 mg, 4.63 mmol), water (4 mL), ammonium chloride (40 mg, 0.74 mmol) and finally ethanol (4 mL). The reaction vial was sealed, and set to heat at 80° C. for twenty hours. The reaction was added to a separatory funnel containing ethyl acetate (100 mL) and brine (75 mL); the phases were separated, and the organic layer was washed again with brine (75 mL). The ethyl acetate layer was then concentrated in vacuo to afford tert-butyl [(1R)-2-(3,4-diaminophenoxy)-1-phenylethyl]carbamate as an orange solid. LRMS (ESI) cale'd for (C19H26N3O3) [M+H]+, 344.2; found 344.2.

Workup

customThe reaction
customvial was sealed
additionThe reaction was added to a separatory funnel
customthe phases were separated
washthe organic layer was washed again with brine (75 mL)
concentrationThe ethyl acetate layer was then concentrated in vacuo

Sources & evidence

ORD record: ord-cb46cb6e813f4908bf1b4e03d80f82e5
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552019B2

Reaction notes

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