Boron tribromide → Methyl 6-(3-hydroxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601914Notes

Reaction equation

HRID 601914 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][CH:7]1[C:11]2[NH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:10]=2[CH2:9][CH2:8]1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][CH:7]1[C:11]2[NH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:10]=2[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59180168Methyl 6-(3-methoxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 59180152Methyl 6-(3-hydroxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 6-(3-methoxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (140 mg, 0.50 mmol) in dry CH2Cl2 (20 mL) was cooled to −78° C., then BBr3, (1.0 M in CH2Cl2) (0.80 mL, 0.80 mmol) was added. The mixture was allowed to warm slowly to room temperature overnight. The mixture was added to saturated sodium bicarbonate, (100 mL) extracted with CH2Cl2, (50 mL) (×3), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The material was purified by chromatography, eluting with heptane-EtOAc, gradient 0 to 50% EtOAc. 50 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.07-2.19 (m, 1H), 2.48-2.74 (m, 4H), 2.90 (dd, J=13.42, 6.30 Hz, 1H), 3.26-3.44 (m, 1H), 3.79 (s, 3H), 6.62 (s, 1H), 6.70 (d, J=1.71 Hz, 1H), 6.72-6.80 (m, 2H), 7.21 (t, J=7.81 Hz, 1H), 8.29 (br. s, 1H).

Workup

  1. extractionextracted with CH2Cl2, (50 mL) (×3)
  2. dry with materialdried (Na2SO4)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe material was purified by chromatography
  5. washeluting with heptane-EtOAc, gradient 0 to 50% EtOAc

Sources & evidence

ORD record
ord-49079adc64f040fa86f25c66846b31c7
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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