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

HRID 661134Notes

Reaction equation

HRID 661134 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 cone 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-1baf45a903404617b0b2bcecf57a8e0d
Source dataset
uspto-grants-2011_12
Patent number
US08084498B2

Reaction notes

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