Methanol → HCID 9869262, compound

HRID 846181Notes

Reaction equation

HRID 846181 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][C:36]=1[O:37]C)[CH2:6][C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][C@@H:19]1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30]C)=[C:26]([O:32]C)[CH:25]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:32][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[OH:30])[CH2:23][C@H:19]1[CH2:20][CH2:21][CH2:22][N:18]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:7]1[CH2:6][C:5]1[CH:34]=[CH:35][C:36]([OH:37])=[C:3]([OH:2])[CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 15044884HCID 15044884, compound

Product 1

HCID 9869262HCID 9869262, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R,R)-1,6-bis-[2-(3,4-dimethoxybenzyl)pyrrolidin-1-yl]hexane (0.001 mol) in dry CH2Cl2 at -70° C. under an inert atmosphere was added BBr3 (4 mL of a 1M solution, 0.004 mol). The reaction mixture was warmed to room temperature, recooled to -70° C., and CH3OH (4 mL) was added. After warming to room temperature, the solvent was removed in vacuo. The residue was subjected to column chromatography, eluting with CH3OH. The fractions containing the desired product were concentrated in vacuo to provide (R,R)-1,6-bis[2-(3,4-dihydroxybenzyl)pyrrolidin-1-yl]hexane, [α]D25 =12.86°.

Workup

  1. customrecooled to -70° C.
  2. temperatureAfter warming to room temperature
  3. customthe solvent was removed in vacuo
  4. washeluting with CH3OH
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-238cdfeaf5854f15ae9fc2ba0aec1de7
Source dataset
uspto-grants-1992_08
Patent number
US05135944

Reaction notes

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