HCID 86731691, compound → TERT-BUTYL (3-AMINO-1,1,1-TRIFLUOROPROPAN-2-YL)CARBAMATE

HRID 1504808Notes

Reaction equation

HRID 1504808 reaction equation
[F:1][C:2]([F:25])([F:24])[CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:4][NH:5]C(=O)OCC1C=CC=CC=1>[Pd].CO>[NH2:5][CH2:4][CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C:2]([F:25])([F:1])[F:24]

Participants

4

Reactant 1

HCID 86731691HCID 86731691, compound

Product 1

HCID 84726007TERT-BUTYL (3-AMINO-1,1,1-TRIFLUOROPROPAN-2-YL)CARBAMATE

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl tert-butyl (3,3,3-trifluoropropane-1,2-diyl)biscarbamate (160 g, 442 mmol) and palladium on carbon (10% w/w, 12 g) in methanol (1500 mL) was stirred at room temperature under a hydrogen atmosphere. After 16 hours, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure, washed with hexane (500 mL), and dried in an oven under reduced pressure to afford tert-butyl (3-amino-1,1,1-trifluoropropan-2-yl)carbamate. MS ESI calc'd. for C8H16F3N2O2 [M+H]+ 229. found 229. 1H NMR (400 MHz, CDCl3) δ 5.30 (d, J=6.8 Hz, 1H), 4.23 (s, 1H), 3.10-2.98 (m, 2H), 1.63 (s, 2H), 1.46 (s, 9H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. washwashed with hexane (500 mL)
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-bffddbd0c8044cbbbbff0b9d2e99d69f
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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