Methanol → HCID 57659862, compound

HRID 601952Notes

Reaction equation

HRID 601952 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[CH2:9][C@@H:10]3[C@H:14]([CH2:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C@@H:11]3[C:12]=2[CH:13]=1)=[O:5])C.[OH-].[Li+].CO>C1COCC1>[CH2:15]([C@H:14]1[C@H:10]2[CH2:9][C:8]3[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:13][C:12]=3[C@@H:11]12)[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180221HCID 59180221, compound

Product 1

HCID 57659862HCID 57659862, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from ±(1S,1aS,5aR)-1-phenethyl-1a,4,5,5a-tetrahydro-1H-4-aza-cyclopropa[α]pentalene-3-carboxylic acid ethyl ester (295 mg, 1.0 mmol) and lithium hydroxide (419 mg, 10.0 mmol in 7 mL water) according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (14 mL) was used. The resulting product was purified by chromatography, eluting with heptane-EtOAc, 0 to 50% EtOAc. 225 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.93-1.06 (m, 1H), 1.07-1.17 (m, 1H), 1.24-1.38 (m, 1H), 1.98 (q, J=6.90 Hz, 1H), 2.20 (t, J=6.74 Hz, 1H), 2.50 (d, J=17.33 Hz, 1H), 2.53-2.61 (m, 2H), 2.88 (dd, J=17.23, 7.13 Hz, 1H), 6.80 (d, J=1.51 Hz, 1H), 7.07 (d, J=7.08 Hz, 2H), 7.16 (d, J=7.32 Hz, 1H), 7.24 (t, J=7.39 Hz, 2H), 8.81 (br. s, 1H). LCMS m/e 268 (M+H). Purity 98% (HPLC).

Workup

  1. customThe resulting product was purified by chromatography
  2. washeluting with heptane-EtOAc, 0 to 50% EtOAc

Sources & evidence

ORD record
ord-f1a8e6be83fe42e2a1e82d8c6ecaf83d
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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