Formic Acid → HCID 90404956, compound

HRID 2277033Notes

Reaction equation

HRID 2277033 reaction equation
C(O)=O.CCN(CC)CC.[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([C:25](=[O:29])[CH2:26][C:27]#[N:28])[CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([C@H:25]([OH:29])[CH2:26][C:27]#[N:28])[CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 58089020HCID 58089020, compound

Product 1

HCID 90404956HCID 90404956, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HCOOH (30.75 mL, 795 mmol) was added dropwise to a cooled (0° C.) solution of Et3N (41.0 mL, 318 mmol) in EtOAc (400 mL) while maintaining the temperature at 0° C. (R,R)—RuCl-TsDPEN (p-cymene) (100 mg, 0.2 mol %) was added to the reaction mixture followed by the addition of oxonitrile (3) (40.0 g, 159 mmol) and the reaction mixture was stirred at room temperature for 24 h. NaHCO3 (10%, 500 mL) was added and the mixture was extracted with EtOAc (500 mL). Organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give (R)-3-(3-(benzyloxy)phenyl)-3-hydroxypropanenitrile (4) as a pale yellow solid. Yield (38.0 g, 95%); 1H NMR (400 MHz, DMSO-d6) δ 7.46-7.44 (m, 2H), 7.41-7.37 (m, 2H), 7.33 (t, J=7.2 Hz, 1H), 7.26 (t, J=8.0 Hz, 1H), 7.07 (s, 1H), 6.99 (d, J=7.6 Hz, 1H), 6.92 (d, J=8.0 Hz, 1H), 5.95 (d, J=4.4 Hz, 1H), 5.09 (s, 2H), 4.86 (d, J=5.2 Hz, 1H), 2.90 (dd, J=16.8, 4.8 Hz, 1H), 2.80 (dd, J=16.8, 6.8 Hz, 1H).

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with EtOAc (500 mL)
  3. dry with materialOrganic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02e3843836314cd98d1ad8974b5d5ab5
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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