Dimethylformamide → Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate
Reaction equation
[C:1]1(S([C@@](C(O)=O)(CO)N)(=O)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)C=CC=1.C1C=CC2N([OH:30])N=NC=2C=1.CCN=C=NC[CH2:37][CH2:38]N(C)C.CN1[CH2:48][CH2:47][O:46]CC1.[CH3:49][N:50]([CH:52]=[O:53])[CH3:51]>>[C:52]([N:50]1[CH2:51][CH2:38][CH2:37][CH:48]([CH2:47][OH:46])[CH2:49]1)([O:30][CH2:1][C:10]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:53]Participants
6
Procedure
To a solution of 2-naphthalene sulfonyl-serine (prepared in Example XII Part D) (0.78 g, 2.67 mmol) and HOBT (0.4 g, 2.93 mmol) in 11 mL DMF was added WSC (0.56 g, 2.93 mmol), followed by Part D compound (1.03 g, 2.67 mmol). After 5 minutes, NMM (0.82 mL, 5.86 mmol) was added to adjust the pH to 7.5-8.0 and the reaction stirred at room temperature for 16 hrs. The reaction mixture was partitioned between EtOAc and a sat. solution of NaHCO3 and the EtOAc layer was washed with a sat. solution of KHSO4, brine, dried over Na2SO4. The organic layer was concentrated in vacuo to give title compound (87% yield). ##STR127##
Workup
- customThe reaction mixture was partitioned between EtOAc
- washa sat. solution of NaHCO3 and the EtOAc layer was washed with a sat. solution of KHSO4, brine
- dry with materialdried over Na2SO4
- concentrationThe organic layer was concentrated in vacuo
Sources & evidence
- ORD record
- ord-dca91c5a3b63424fb5f88d6b58e8556f
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05583146
Reaction notes
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