Water → HCID 57794767, compound

HRID 2099288Notes

Reaction equation

HRID 2099288 reaction equation
C1(C)C=CC=CC=1.[C:8]1([C@@:14]2([C:26]#N)[CH2:16][C@H:15]2[CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].C([Al+]CC(C)C)C(C)C.[OH2:38]>O1CCCC1>[C:8]1([C@@:14]2([CH:26]=[O:38])[CH2:16][C@H:15]2[CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 21225700DiisobutylaluminumhydrideHCID 57794765HCID 57794765, compound

Product 1

HCID 57794767HCID 57794767, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 300 mL toluene and (1R,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropanecarbonitrile (12.0 g, 45.57 mmol, 1 eq), accessed via the method of Preparation 3B, at 0° C. was added 59.3 mL 1M diisobutylaluminum hydride (59.3 mmol, 1.3 eq) in tetrahydrofuran. The mixture was stirred at 0° C. for 4 h and then at ambient temperature for 18 h before dilution with 500 mL toluene and 500 mL water. The mixture was stirred for 30 min and then filtered through a pad of celite. The organics were isolated, dried over Na2SO4, filtered and concentrated to give the title compound (7.8 g, 29.3 mmol, 64%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 9.39 (s, 1H), 7.39-7.19 (m, 10H), 4.33-4.23 (m, 2H), 3.36-3.33 (m, 1H), 3.03-2.98 (m, 1H), 2.16-2.11(m, 1H), 1.77-1.73 (m, 1H), 1.46-1.43 (m, 1H).

Workup

  1. stirringThe mixture was stirred for 30 min
  2. filtrationfiltered through a pad of celite
  3. customThe organics were isolated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-617341c74b204df7a8652d99ff464d02
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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