Lithium Hydroxide → HCID 22622412, compound

HRID 840427Notes

Reaction equation

HRID 840427 reaction equation
B.[OH:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[CH2:16][CH2:15][N:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]1)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.ClC1C=C([C@H](CCN2CCC(C3C=CC=CC=3C(OC)=O)CC2)CN(C)C(C2C3C(=CC=CC=3)C=C(C#N)C=2)=O)C=CC=1Cl.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.[OH-].[Li+]>O1CCCC1>[OH:2][CH2:3][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[CH2:16][CH2:15][N:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]1

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 6331BoraneHCID 90495Di-tert-butyl dicarbonateHCID 18715647HCID 18715647, compoundHCID 22622404HCID 22622404, compound

Product 1

HCID 22622412HCID 22622412, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M borane solution in tetrahydrofuran (6 mL) was added to a solution of tert-butyl 4-(2-hydroxycarbonylphenyl)piperidinecarbamate (0.915 g) (prepared from 4-(2-methoxycarbonylphenyl)piperidine [Example 20] by N-protection using di-tert-butyldicarbonate followed by saponification of the methyl ester with lithium hydroxide) in tetrahydrofuran (20 mL) at 0° C. The reaction was warmed to ambient temperature and stirred overnight. The reaction was quenched with methanol and 1N aqueous HCl then extracted with diethyl ether. The organic phase was separated and extracted sequentially with aqueous sodium bicarbonate and brine. The organic phase was dried and evaporated to give the title compound (0.906 g) as a colorless oil. MS: m/z=192 (M-Boc). 1H NMR (CDCl3) δ 7.28 (m, 4H, Ar—H), 4.75 (d, 2H, Ar—CH2—O), 3.05 (m, 1H), 2.83 (m, 3H), 1.70 (m, 5H), 1.49 (s, 9H).

Workup

  1. customat 0° C
  2. customThe reaction was quenched with methanol and 1N aqueous HCl
  3. extractionthen extracted with diethyl ether
  4. customThe organic phase was separated
  5. extractionextracted sequentially with aqueous sodium bicarbonate and brine
  6. customThe organic phase was dried
  7. customevaporated

Sources & evidence

ORD record
ord-76949c340e9f475fb8ed63b492d77097
Source dataset
uspto-grants-2002_04
Patent number
US06365602B1

Reaction notes

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