Sodium Bicarbonate → HCID 25222789, compound

HRID 43360Notes

Reaction equation

HRID 43360 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:25])[CH2:16][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH3:26][C@@H:27]1[CH2:32][NH:31][CH2:30][C@H:29]([CH3:33])[N:28]1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15](=[O:25])[CH2:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:21][N:31]4[CH2:32][C@H:27]([CH3:26])[N:28]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C@H:29]([CH3:33])[CH2:30]4)=[CH:23][CH:24]=3)[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21021901tert-Butyl (2R,6S)-2,6-dimethylpiperazine-1-carboxylateHCID 252238954-(2-{4-[(4-Fluorophenyl)amino]-1-piperidinyl}-2-oxoethyl)benzaldehyde

Product 1

HCID 25222789HCID 25222789, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of D4 (149 mg, 0.438 mmol) and 1,1-dimethylethyl (2R,6S)-2,6-dimethyl-1-piperazinecarboxylate (94 mg, 0.438 mmol) in 1,2-DCE (3 ml) was stirred for 5 mins at room temperature. Sodium tri(acetoxy)borohydride (139 mg, 0.66 mmol) was added and the mixture was stirred for 3 h then saturated aq. NaHCO3 solution was added. The mixture was stirred for 15 mins then extracted with EtOAc. The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product which was purified by chromatography. Elution with 20-90% EtOAc/pentane gave 1,1-dimethylethyl (2R,6S)-4-{[4-(2-{4-[(4-fluorophenyl)amino]-1-piperidinyl}-2-oxoethyl)phenyl]methyl}-2,6-dimethyl-1-piperazinecarboxylate (143 mg). δH (CDCl3, 400 MHz) 1.06 (1H, m), 1.27 (6H, d), 1.30 (1H, m), 1.46 (9H, s), 1.93 (1H, m), 2.05 (1H, m), 2.12 (2H, dd), 2.59 (2H, d), 2.88 (1H, m), 3.13 (1H, m), 3.29 (1H, m), 3.38 (1H, m), 3.45 (2H, s), 3.74 (2H, s), 3.86 (1H, m), 4.07 (2H, m), 4.50 (1H, m), 6.50 (2H, m), 6.87 (2H, t), 7.20 (2H, m), 7.31 (2H, d). MS (ES): MH+ 539

Workup

  1. stirringthe mixture was stirred for 3 h
  2. stirringThe mixture was stirred for 15 mins
  3. extractionthen extracted with EtOAc
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product which
  7. customwas purified by chromatography
  8. washElution with 20-90% EtOAc/pentane

Sources & evidence

ORD record
ord-7333b5b120c74da185ba41ee510770e1
Source dataset
uspto-grants-2013_09
Patent number
US08536182B2

Reaction notes

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