Benzyl Alcohol → HCID 67108470, compound

HRID 471887Notes

Reaction equation

HRID 471887 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C:16]3([CH2:23][CH2:22][CH2:21][CH:20](C(O)=O)[CH2:19]3)[C:15]2=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NC1CC[N:32]([C:35]([O:37][C:38]([CH3:41])(C)C)=[O:36])CC1.C(N(CC)CC)C.C(O)[C:50]1[CH:55]=[CH:54]C=[CH:52][CH:51]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C:16]3([CH2:23][CH2:22][CH2:21][CH:20]([NH:32][C:35]([O:37][CH2:38][C:41]4[CH:54]=[CH:55][CH:50]=[CH:51][CH:52]=4)=[O:36])[CH2:19]3)[C:15]2=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 58237135HCID 58237135, compound2×

Product 1

HCID 67108470HCID 67108470, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using the same experimental procedures described in the synthesis of intermediate 10, 2-(1-tert-Butoxycarbonyl-piperidin-4-yl)-1-oxo-2-aza-spiro[4.5]decane-7-carboxylic acid (mixture of cis and trans diastereomers) was made from 7.40 mmol of 1-(2-oxo-ethyl)-cyclohexane-1,3-dicarboxylic aid diethyl ester and 7.40 mmol of 4-amino-1-Boc-piperidine. 2-(1-tert-Butoxycarbonyl-piperidin-4-yl)-1-oxo-2-aza-spiro[4.5]decane-7-carboxylic acid (1.24 g, 3.25 mmol) was dissolved in toluene (20.0 mL), triethylamine (0.54 mL, 3.90 mmol) was added, followed by the addition of diphenylphosphonic azid (0.70 mL, 3.25 mmol). The mixture was stirred at rt for 1.5 hrs, and then heated at 90° C. for 2 hrs. Benzyl alcohol (2.0 mL, 19.5 mmol) was added, and the mixture was heated at 90° C. overnight. The mixture was cooled down, concentrated under reduce pressure to afford 0.85 g (54%) of the title compound which is a mixture of two diastereomers (cis/trns: 1/1; under LC-MS method C, the first peak with RT of 1.56 min was assigned as cis, and the second peak with RT of 1.59 min was assigned as trans.). ESI-MS m/z: 486 (M+H)+.

Workup

  1. temperatureheated at 90° C. for 2 hrs
  2. temperaturethe mixture was heated at 90° C. overnight
  3. temperatureThe mixture was cooled down
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cfe9b07befa247fab01cf329039bd8bb
Source dataset
uspto-grants-2014_01
Patent number
US08633190B2

Reaction notes

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