Phenol → Benzyl 3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-(4-phenoxymethylphenyl)piperidine-1-carboxylate
Reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])[CH2:25][CH:24]2[O:39][CH2:40][C:41]2[CH:42]=[CH:43][C:44]3[O:49][CH2:48][CH2:47][N:46]([CH2:50][CH2:51][CH2:52][O:53][CH3:54])[C:45]=3[CH:55]=2)=[CH:19][CH:18]=1.[C:56]1(O)[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH3:54][O:53][CH2:52][CH2:51][CH2:50][N:46]1[C:45]2[CH:55]=[C:41]([CH2:40][O:39][CH:24]3[CH:23]([C:20]4[CH:19]=[CH:18][C:17]([CH2:16][O:15][C:56]5[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=5)=[CH:22][CH:21]=4)[CH2:28][CH2:27][N:26]([C:29]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:30])[CH2:25]3)[CH:42]=[CH:43][C:44]=2[O:49][CH2:48][CH2:47]1Participants
5
Procedure
0.0819 g of diisopropyl azodicarboxylate is added dropwise to a solution of 0.180 g of benzyl 4-(4-hydroxymethylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate (Example 270c), 0.0304 g of phenol and 0.102 g of triphenylphosphine. The solution is stirred at room temperature for 1 hour and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.25 (1:2 EtOAc-heptane); Rt=5.99.
Workup
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-d944a0e20fa248c396fa90834fe0f58a
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842688B2
Reaction notes
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