Di-tert-butyl dicarbonate → Tert-butyl{2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropyl}carbamate

HRID 2194922Notes

Reaction equation

HRID 2194922 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[C:19]#[N:20])=[C:14]([CH3:28])[CH:13]=1.[O:29](C(OC(C)(C)C)=O)[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=O.[BH4-].[Na+]>CCO.C1COCC1>[C:33]([O:32][C:30](=[O:29])[NH:20][CH2:19][CH:18]([C:15]1[CH:16]=[CH:17][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:13][C:14]=1[CH3:28])[CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 4311764Sodium borohydrideHCID 674474272-[2'-(3-Methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropanenitrile

Product 1

HCID 131730115Tert-butyl{2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropyl}carbamate

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 2-[2′-(3-methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropanenitrile from step 2 (1 eq.) in EtOH/THF (3:1; 0.1M) at room temperature was added cobaltous chloride hexahydrate (CoCl2.6H2O; 2 eq.), followed by (BOC)2O (2 eq.) and finally sodium borohydride (10 eq.) portionwise. The final black mixture was stirred for 3 h at room temperature, quenched with HCl (1N). The pH was adjusted to 8 using saturated aqueous Na2CO3 and the resulting mixture was extracted several times with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (10 to 75% in 30 min) afforded the desired compound as a colorless oil.

Workup

  1. customquenched with HCl (1N)
  2. extractionthe resulting mixture was extracted several times with EtOAc
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  7. washeluting with Hex/EtOAc (10 to 75% in 30 min)

Sources & evidence

ORD record
ord-286d156192604ba6ae476c5bd7f162ee
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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