Hydrazine hydrate (1:1) → Tert-butyl 3-amino-3-phenylpropylcarbamate

HRID 1186505Notes

Reaction equation

HRID 1186505 reaction equation
O.NN.[C:4]([O:8][C:9](=[O:31])[NH:10][CH2:11][CH2:12][CH:13]([N:20]1C(=O)C2C(=CC=CC=2)C1=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:7])([CH3:6])[CH3:5]>C1COCC1.CO>[C:4]([O:8][C:9](=[O:31])[NH:10][CH2:11][CH2:12][CH:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 578268242-[3-(Boc-amino)-1-phenylpropyl]isoindoline-1,3-dione

Product 1

HCID 57826906Tert-butyl 3-amino-3-phenylpropylcarbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Hydrazine hydrate (85%, 5.1 mL, 74 mmol) was added to a solution of [3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propyl]-carbamic acid tert-butyl ester (2.8 g, 7.4 mmol) in THF (25 mL) and MeOH (25 mL). The resulting mixture was heated to 65° C. for 6 hours. Then the precipitate was filtered, and the filtrate was concentrated under reduced pressure to give crude product which was purified by column chromatography on silica gel (dichloromethane:MeOH, 100:1, 1% NH3 H2O) to give (3-amino-3-phenyl-propyl)-carbamic acid tert-butyl ester as an off-white solid. (Yield 1.7 g, 92%). 1H NMR (300 MHz, CDCl3): δ 7.31-7.18 (m, 5H), 6.82 (brs, 1H), 3.78-3.74 (m, 1H), 2.92 (brs, 2H), 1.82 (s, 2H), 1.63-1.61 (m, 2H), 1.37 (s, 9H). LC-MS: [M+H]+ 251.

Workup

  1. filtrationThen the precipitate was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give crude product which
  4. customwas purified by column chromatography on silica gel (dichloromethane:MeOH, 100:1, 1% NH3 H2O)

Sources & evidence

ORD record
ord-dbf36edb01634a48a5c924bfa232cb15
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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