Sodium Carbonate → HCID 15454928, compound

HRID 2287532Notes

Reaction equation

HRID 2287532 reaction equation
[NH2:1][C@H:2]1[CH2:7][C@H:6]([CH2:8][OH:9])[CH2:5][N:4]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C@H:3]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][C:29]=1[CH:30]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:13]([O:12][C:10]([N:4]1[CH2:5][C@@H:6]([CH2:8][OH:9])[CH2:7][C@H:2]([NH:1][CH2:30][C:29]2[CH:32]=[C:33]([O:36][C:37]([F:38])([F:39])[F:40])[CH:34]=[CH:35][C:28]=2[O:27][CH3:26])[C@@H:3]1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 15454926HCID 15454926, compound

Product 1

HCID 15454928HCID 15454928, compoundYield 121.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2S*,3S*,5S*)-3-amino-1-benzyloxycarbonyl-5-hydroxymethyl-2-phenylpiperidine (0.50 g, 1.36 mmol)) and 2-methoxy-5-trifluoromethoxybenzaldehyde (0.37 g, 1.70 mmol) in CH2Cl2 (20.0 ml) was added NaB(OAc)3H (0.43 g, 2.04 mmol) portionwise. The reaction mixture was stirred at room temperature for 3 hours, and then basified with sat. Na2CO3 aq. solution. The mixture was extracted with CH2Cl2. The combined extracts were dried (Na2SO4), and concentrated in vacuo to give a red oil (0.90 g), which solidified spontaneously on standing in a refrigerator (4 C.). This was flash chromatographed over SiO2 (Merck Kieselgel 60, 18.0 g). Elution with CH2Cl2 --MeOH (300:1/200:1/100:1) gave title compound (0.678 g, 91.6%) as a colorless syrup. IRmax (film): 3450(s), 1698(s), 1682(s), 1670(s), 1498(s), 1230(br., s), 1160(br., s), 1030(s), 738(s), 700(s) cm31 1 ; 1H-NMR δ: 7.44-7.21(m, 9H), 7.18(br.s, 1H), 7.04(br.d, J=8.8 Hz, 1H), 7.00(br.s, 1H), 6.92(d, J=8.8 Hz, 1H), 5.40-5.27(m, 1H), 5.17(d, J=121.5 Hz, 1H), 5.05(d, J=12.5 Hz, 1H), 4.03(br.d, J=13.9 Hz, 1H), 3.74(d, J=13.9 Hz, 1H), 3.70-3.41(m, 4H), 3.62(s, 3H), 3.23-3.11(m, 1H), 2.20-1.95(m, 2H), 1.70-1.45(m, 3H) ppm.

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c69fae095ced4536920c88982c32bf5a
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

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