Water → HCID 69747005, compound

HRID 497474Notes

Reaction equation

HRID 497474 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH2:14])[C@@H:10]([C:15]([OH:17])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C@@H:10]([C:15]([OH:17])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 69747091HCID 69747091, compound

Product 1

HCID 69747005HCID 69747005, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dry flask (3S,4R)-4-aminopiperidine-1,3-dicarboxylic acid 1-tert-butyl ester (1.32 g, 5.40 mmol) was dissolved in dichloromethane (30 mL) and triethylamine (1.0 mL, 7.2 mmol) and benzyl chloroformate (0.94 mL, 5.9 mmol) were added. The mixture was stirred for 18 hours. Water (30 mL) was added and the layers separated. The aqueous layer was extracted with dichloromethane (30 mL). The combined organic layers were washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo to give a crude oil (2.13 g). Purification by flash column chromatography (5-20% methanol/chloroform) provided a colorless oil (1.29 g, 63%). 1H NMR (400 MHz, DMSO-d6, 120° C.), δ: 7.34 (m, 5H), 6.76 (bs, 1H), 5.04 (s, 2H), 4.01, (bs, 1H), 3.78 (dd, J=14, J′=7, 1H), 3.47 (m, 2H), 3.26 (m, 1H), 2.67 (dt, J=7, J′=4, 1H), 2.49 (m, 1H), 1.79 (m, 1H), 1.59 (m, 1H), 1.40 (s, 9H). MS (ESI), m+/z: (M+Na)+=401.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with dichloromethane (30 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude oil (2.13 g)
  8. customPurification by flash column chromatography (5-20% methanol/chloroform)

Sources & evidence

ORD record
ord-368ab638bc304e85954088de4286523a
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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