(1-Ethoxycyclopropoxy)trimethylsilane → HCID 58993542, compound

HRID 391482Notes

Reaction equation

HRID 391482 reaction equation
[C:1]1([C:7]2([CH2:13][O:14][CH2:15][C:16]3[CH:17]=[C:18]([C:26]4[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=4)[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[C:37]1(O[Si](C)(C)C)[CH2:39][CH2:38]1)C.C([BH3-])#N.[Na+]>>[CH:37]1([N:10]2[CH2:11][CH2:12][C:7]([CH2:13][O:14][CH2:15][C:16]3[CH:17]=[C:18]([C:26]4[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=4)[CH:19]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:21]=3)([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9]2)[CH2:39][CH2:38]1

Participants

4

Reactant 3

HCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 24785978HCID 24785978, compound

Product 1

HCID 58993542HCID 58993542, compound

Conditions

Temperature
90 °C

Procedure

A microwave tube was charged with 3′-(((4-phenylpiperidin-4-yl)methoxy)methyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (21.5 mg, 0.05 mmol), (1-ethoxycyclopropoxy)trimethylsilane (96.5 μL, 0.47 mmol), sodium cyanoborohydride (15 mg, 0.24 mmol). The tube was flushed with nitrogen and treated with methanol (2 mL) and acetic acid (3 drops). The tube was sealed and heated at 90° C. for 1 h via microwave. After cooling, the reaction was concentrated and purified by flash chromatography on silica gel (10% methanol/methylene chloride) to afford 13.5 mg (55%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.76 (s, 1H), 7.74 (s, 1H), 7.66 (s, 1H), 7.60 (s, 1H), 7.58 (s, 1H), 7.42 (s, 1H), 7.33-7.37 (m, 5H), 7.21-7.24 (m, 1H), 4.45 (s, 2H), 3.44 (s, 2H), 3.11-3.14 (m, 2H), 2.56-2.61 (m, 2H), 2.35-2.38 (m, 2H), 2.09-2.16 (m, 2H), 1.78-1.79 (m, 1H), 0.82 (m, 2H), 0.54-0.56 (m, 2H). Mass spec.: 491.44 (MH)+. Accurate mass spec.: m/z 491.2331 [MH]+, Δ=4.2 ppm.

Workup

  1. customThe tube was flushed with nitrogen
  2. additiontreated with methanol (2 mL) and acetic acid (3 drops)
  3. customThe tube was sealed
  4. temperatureAfter cooling
  5. concentrationthe reaction was concentrated
  6. custompurified by flash chromatography on silica gel (10% methanol/methylene chloride)
  7. customto afford 13.5 mg (55%) as a colorless oil

Sources & evidence

ORD record
ord-cb8d9b79ef5a407d918bd35e7e7f1c30
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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