Hydrazine hydrate (1:1) → (R)-tert-butyl 1-aminobut-3-en-2-yl(benzyloxy)carbamate

HRID 627179Notes

Reaction equation

HRID 627179 reaction equation
[CH2:1]([O:8][N:9]([C@H:17]([CH:30]=[CH2:31])[CH2:18][N:19]1C(=O)C2C(=CC=CC=2)C1=O)[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO.CCOCC>[NH2:19][CH2:18][C@H:17]([N:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:30]=[CH2:31]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117940062(R)-tert-butyl benzyloxy(1-(1,3-dioxoisoindolin-2-yl)but-3-en-2-yl)carbamate2×

Product 1

HCID 89863084(R)-tert-butyl 1-aminobut-3-en-2-yl(benzyloxy)carbamateYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of (R)-tert-butyl benzyloxy(1-(1,3-dioxoisoindolin-2-yl)but-3-en-2-yl)carbamate (Intermediate 155, 80 g, 189.36 mmol) and hydrazine hydrate (47.4 g, 946.86 mmol) in MeOH (800 mL) was stirred at rt overnight. The mixture was diluted with ether and filtered. The filtrate was evaporated and the residue was purified by silica gel column and eluted with MeOH/DCM (0-10%) to give the title compound (44.3 g, 80%) as a colorless oil.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe residue was purified by silica gel column
  4. washeluted with MeOH/DCM (0-10%)

Sources & evidence

ORD record
ord-200c1dd28f3c499982887495a7f33e94
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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