Methanol → 4-(1,1-Dimethylethyl) 1-(phenylmethyl) 2-(hydroxymethyl)-1,4-piperazinedicarboxylate

HRID 2371187Notes

Reaction equation

HRID 2371187 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[C:24](O)=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.CO>C1COCC1>[OH:25][CH2:24][CH:12]1[CH2:13][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH2:15][CH2:16][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 2756777N-4-Boc-N-1-Cbz-2-piperazine carboxylic acid

Product 1

HCID 235310394-(1,1-Dimethylethyl) 1-(phenylmethyl) 2-(hydroxymethyl)-1,4-piperazinedicarboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1-[(benzyloxy)carbonyl]-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1 g) in anhydrous THF (11 ml) under argon, cooled to 0° C. was added 1M borane in THF (11 ml) and the mixture allowed to warm to room temperature over 3.5 hours. After cooling to 0° C., MeOH was added and stirring continued for 72 hours. The solvents were evaporated, saturated aqueous sodium bicarbonate and ethyl acetate added, the organic phase dried (MgSO4) and evaporated to give the title compound (0.88 g, 92%).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customThe solvents were evaporated
  3. additionsaturated aqueous sodium bicarbonate and ethyl acetate added
  4. dry with materialthe organic phase dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-2193abe0ede94f3c972a318ead6ee0bb
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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