Hydrochloric Acid → Ethyl 11-[1-(t-butoxycarbonyl)cyclopropyl]-2,2-dimethyl-7-oxoundecanoate

HRID 969001Notes

Reaction equation

HRID 969001 reaction equation
Cl.[C:2]([O:6][C:7]([C:9]1([CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:31])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]2([C:24]([O:26][C:27](C)(C)[CH3:28])=[O:25])[CH2:23][CH2:22]2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3]>>[C:2]([O:6][C:7]([C:9]1([CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:31])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:23])([CH3:22])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 21932031t-Butyl 1-[9-[1-(tert-butoxycarbonyl)cyclopropyl]-5-oxononyl]-1-cyclopropanecarboxylate

Product 1

HCID 21932028Ethyl 11-[1-(t-butoxycarbonyl)cyclopropyl]-2,2-dimethyl-7-oxoundecanoate

Procedure

Compound 6c was prepared likewise Method C starting from 108a (20.5 g, 55.9 mmol), 105a (18.11 g, 55.9 mmol) and KOtBu (6.57 g, 58.7 mmol) to give a yellow oil (31.79 g). Part of this oil (30.63 g) was treated with conc aqueous HCl (23 mL), as described for 106d, to give, after purification by column chromatography (silica, heptane:EtOAc=40:1), 106c (9.83 g, >90% pure by NMR, 43%) as a colorless oil. 1H NMR: δ 4.09 (q, J=7.2 Hz, 2H), 2.38 (t, J=7.2 Hz, 4H), 1.62-1.35 (m, 10H), 1.41 (s, 9H), 1.26-1.17 (m, 2H), 1.24 (t, J=7.2 Hz, 3H), 1.14 (s, 6H), 1.09 (dd, J=6.9, 4.2 Hz, 2H), 0.59 (dd, J=6.3, 3.6 Hz, 2H). 13C NMR: δ 210.5, 177.4, 174.0, 79.8, 60.2, 42.8, 42.6, 42.1, 40.5, 34.0, 28.2 (3×), 27.5, 25.2 (2×), 24.7, 24.3, 24.2, 24.1, 15.3 (2×), 14.4.

Workup

  1. customto give
  2. customafter purification by column chromatography (silica, heptane:EtOAc=40:1), 106c (9.83 g, >90% pure by NMR, 43%) as a colorless oil

Sources & evidence

ORD record
ord-f1ac9880010a4c0c8f3df9fa28d05f51
Source dataset
uspto-grants-2007_12
Patent number
US07304093B2

Reaction notes

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