Hydrochloric Acid → (3S*,5R*)-5-Amino-piperidine-1,3-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester, hydrochloride

HRID 1698300Notes

Reaction equation

HRID 1698300 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C@H:22]([NH:24]C(OC(C)(C)C)=O)[CH2:21][C@H:20]([C:32]([OH:34])=[O:33])[CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[ClH:35].CCCCCC>O1CCOCC1>[ClH:35].[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C@H:22]([NH2:24])[CH2:21][C@H:20]([C:32]([OH:34])=[O:33])[CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 57870323HCID 57870323, compound2×

Product 1

HCID 69239345(3S*,5R*)-5-Amino-piperidine-1,3-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester, hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of (3S*,5R*)-5-tert-butoxycarbonylamino-piperidine-1,3-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (4.7 g, 10.1 mmol) (see Starting Material 1 above) in dioxane (25 mL), HCl (4M in dioxane, 25 mL, 100 mmol) is added and the reaction mixture is stirred for 16 h at RT. Hexane (50 mL) is added and the crystals are filtered off, washed with hexane and dried in vacuo to afford the title compound as a white solid. MS: 367.4 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 4.48 min.

Workup

  1. additionis added
  2. filtrationthe crystals are filtered off
  3. washwashed with hexane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-eb308637624649adb0cc33039aab7ebf
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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