Bromopinacolone → HCID 178495788, compound

HRID 255139Notes

Reaction equation

HRID 255139 reaction equation
[CH2:1]1[CH:8]2[C:4]3([C:10]([NH:12][C:13]([NH:15][CH2:16][CH2:17][O:18][CH3:19])=[S:14])=[O:11])[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2.Br[CH2:21][C:22](=O)[C:23]([CH3:26])([CH3:25])[CH3:24]>>[C:23]([C:22]1[N:15]([CH2:16][CH2:17][O:18][CH3:19])/[C:13](=[N:12]/[C:10]([C:4]23[CH2:5][CH:6]4[CH2:9][CH:2]([CH2:1][CH:8]2[CH2:7]4)[CH2:3]3)=[O:11])/[S:14][CH:21]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 21642BromopinacoloneHCID 866524581-(Hexahydro-2,5-methano-pentalene-3a-carbonyl)-3-(2-methoxyethyl)-thiourea

Product 1

HCID 178495788HCID 178495788, compound

Procedure

A mixture of Example 14B (57 mg, 0.20 mmol) and 1-bromo-3,3-dimethyl-butan-2-one (36 mg, 0.027 mL, 0.20 mmol, Aldrich) was processed according to the method described in Example 14C. Purification by column chromatography (SiO2, 30-45% ethyl acetate/hexanes gradient) afforded title compound. 1H NMR (dimethylsulfoxide-d6 300 MHz) δ 1.37 (s, 9 H), 1.56-1.63 (m, 4 H), 1.69-1.79 (m, 4 H), 2.07-2.18 (m, 2 H), 2.24-2.30 (m, 2 H), 2.53-2.60 (m, 1 H), 3.26 (s, 3 H), 3.75 (t, J=6.78 Hz, 2 H), 4.40 (t, J=6.95 Hz, 2 H), 6.57 (s, 1 H); MS (DCI/NH3) m/z 363 (M+H)+.

Workup

  1. customPurification by column chromatography (SiO2, 30-45% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-2a84df6e98e94bdc92329be161f6a915
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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