Sodium Bicarbonate → HCID 69158017, compound

HRID 967399Notes

Reaction equation

HRID 967399 reaction equation
C(O[C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[NH2:13])C.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.C(O)(=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([N:13]2[C:7]3[C:6](=[CH:11][C:10]([Cl:12])=[CH:9][CH:8]=3)[CH2:5][C:4]2=[O:14])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 69159126HCID 69159126, compound

Product 1

HCID 69158017HCID 69158017, compoundYield 138.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

(2-Amino-5-chloro-phenyl)-acetic acid ethyl ester (3.3 g, 15.4 mmol), 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (4.6 g, 23 mmol) were set stirring in CH2Cl2 (50 mL) and sodium triacetoxyborohydride (4.9 g, 23.1 mmol) was added followed by acetic acid (3 mL). After 5 days saturated NaHCO3 was added and the organics separated. The organics were dried (MgSO4) and evaporated to give 7.5 g of a clear golden oil. The oil was purified (silica, 50% EtOAc/hexanes) to give 3.4 g (63%) of a white solid. TLC (silica, 25% EtOAc/hexanes): Rf=0.18. MS (electrospray): exact mass calculated for C18H23ClN2O3, 350.14. m/z found, 373.1 [M+Na]+. 1H NMR (400 MHz, CDCl3): 7.40-7.30 (m, 2H), 7.00 (d, J=8.4 Hz, 1H), 4.55-4.45 (m, 1H), 4.40 (m, 2H), 3.63 (s, 2H), 2.94 (m, 2H), 2.45-2.30 (m, 2H), 1.82 (m, 2H), 1.62 (s, 9H).

Workup

  1. dry with materialThe organics were dried (MgSO4)
  2. customevaporated

Sources & evidence

ORD record
ord-e935a2f5f01149c4bda3f28e9ddb4078
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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