Hydrochloric Acid → HCID 131723701, compound

HRID 2298101Notes

Reaction equation

HRID 2298101 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[OH:25][CH2:26][CH:27]1[NH:32][CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>CO.O1CCOCC1.ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:32]2[CH2:31][CH2:30][NH:29][CH2:28][CH:27]2[CH2:26][OH:25])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 18381537HCID 18381537, compoundHCID 223865084-N-Boc-2-hydroxymethylpiperazine

Product 1

HCID 131723701HCID 131723701, compoundYield 24.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Prepared according to the method described in Example 66c from 2-chloro-5-(2-oxoethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.094 g, Example 66b), 3-(hydroxymethyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (0.117 g), sodium triacetoxyborohydride (0.081 g) and 1,2-dichloroethane (2 ml). After work-up, the residue was purified by HPLC eluting with a gradient of 0-5% ethanol in dichloromethane then chromatography eluting with ethyl acetate then ethyl acetate: ethanol (95:5). The white powder obtained was dissolved in methanol (2 ml) and a solution of hydrochloric acid in dioxane (4N, 1 ml) was added. The mixture was stirred for 14 h at room temperature. Solvents were then removed under reduced pressure and the product obtained was triturated with diethyl ether to afford the title compound as a white powder (0.016 g).

Workup

  1. customPrepared
  2. customAfter work-up, the residue was purified by HPLC
  3. washeluting with a gradient of 0-5% ethanol in dichloromethane
  4. washchromatography eluting with ethyl acetate
  5. customThe white powder obtained
  6. customSolvents were then removed under reduced pressure
  7. customthe product obtained
  8. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-6f0f3663415646edad1950f1d655ad7c
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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