Hydrochloric Acid → HCID 68680811, compound

HRID 2245834Notes

Reaction equation

HRID 2245834 reaction equation
[Si](O[CH2:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH:19]([O:22]C)OC)[C:13]1=[O:24])(C(C)(C)C)(C)C.Cl.[NH:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33](=[O:47])[NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:28][CH2:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(#N)C>[OH:22][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][N:12]([CH2:11][CH2:10][CH2:9][N:26]2[CH2:27][CH2:28][CH:29]([O:32][C:33](=[O:47])[NH:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:30][CH2:31]2)[C:13]1=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 10851461Biphenyl-2-ylcarbamic Acid Piperidin-4-yl EsterHCID 68680479HCID 68680479, compound

Product 1

HCID 68680811HCID 68680811, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To crude 1-[3-(tert-butyldimethylsilanyloxy)propyl]-3-(3,3-dimethoxypropyl)imidazolidin-2-one (11.4 g, 32 mmol; prepared as described in Preparation 2) was added to a 1:1 mixture of 1N aqueous HCl (32 mL, 32 mmol, 1.0 eq) in ACN (32 mL). The reaction was allowed to stir at room temperature for 2 hours. To the reaction mixture was added biphenyl-2-ylcarbamic acid piperidin-4-yl ester (9.4 g, 32 mmol; prepared as described in Preparation 3) and was allowed to stir for 30 minutes, followed by the addition of NaBH(OAc)3 (20.3 g, 96 mmol). The reaction mixture was allowed to stir overnight. After overnight, the solution was concentrated in vacuo. The crude mixture was taken up in DCM (400 mL) and washed with 1N NaOH (200 mL), water (200 mL) and brine (200 mL). The organic phase was dried over MgSO4, filtered and concentrated then purified via silica gel chromatography (10% MeOH in DCM with 1% NH3(aq)) to afford the title compound (7.98 g, 16.6 mmol) in 52% yield.

Workup

  1. stirringto stir for 30 minutes
  2. stirringto stir overnight
  3. waitAfter overnight
  4. concentrationthe solution was concentrated in vacuo
  5. washwashed with 1N NaOH (200 mL), water (200 mL) and brine (200 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthen purified via silica gel chromatography (10% MeOH in DCM with 1% NH3(aq))

Sources & evidence

ORD record
ord-e8ec1a0755e648c2a5c656d1e2b0fd18
Source dataset
uspto-grants-2010_03
Patent number
US07683173B2

Reaction notes

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