Accelerator DM → tert-butyl (3RS,4RS)-4-[4-[3-(benzothiazol-2-ylsulfonyl)-propoxy]-phenyl]-3-(1-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

HRID 1005111

Reaction equation

HRID 1005111 reaction equation
COC1C2C(=CC=CC=2)C=CC=1CBr.C1(C)C=C[C:18]([S:21]([O-:24])(=O)=[O:22])=CC=1.[NH+:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O[CH2:33][CH2:34][CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH:43]2[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH:44]2[O:56][CH2:57][C:58]2[CH:67]=[CH:66][C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[C:59]=2[O:68][CH3:69])=[CH:39][CH:38]=1.[S:70]1C2C=CC=CC=2N=[C:71]1SSC1SC2C=CC=CC=2N=1>C(O)C>[S:70]1[C:71]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=2[N:26]=[C:18]1[S:21]([CH2:33][CH2:34][CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH:43]2[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:54])([CH3:55])[CH3:53])=[O:50])[CH2:45][CH:44]2[O:56][CH2:57][C:58]2[CH:67]=[CH:66][C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[C:59]=2[O:68][CH3:69])=[CH:39][CH:38]=1)(=[O:24])=[O:22]

Participants

6

Reactant 4

HCID 8447Accelerator DMHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 221263282-(Bromomethyl)-1-methoxynaphthaleneHCID 86604446tert-butyl (3RS,4RS)-4-[4-(3-hydroxy-propoxy)-phenyl]-3-(1-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

Product 1

HCID 86604445tert-butyl (3RS,4RS)-4-[4-[3-(benzothiazol-2-ylsulfonyl)-propoxy]-phenyl]-3-(1-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In an analogous manner to that described in Example 1 (g), by alkylating a mixture of tert-butyl (3RS,4RS)- and (3SR,4SR)-3-hydroxy-4-[4-[3-[(RS)-tetrahydro-pyran-2-yloxy]-propoxy]-phenyl]-piperidine-1-carboxylate [Example 57 (a)] with 1-methoxy-2-bromomethyl-naphthalene [Example 7 (f)] there was obtained a mixture of tert-butyl (3RS,4RS)- and (3SR,4SR)-3-(1-methoxy-naphthalen-2-ylmethoxy)-4-[4-[3-[(RS)-tetrahydro-pyran-2-yloxy]-propoxy]-phenyl]-piperidine-1-carboxylate. Cleavage of the THP group by means of pyridinium (toluene-4-sulphonate) in ethanol analogously to Example 53 (c) gave tert-butyl (3RS,4RS)-4-[4-(3-hydroxy-propoxy)-phenyl]-3-(1-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate, reaction of which with bis-(benzothiazol-2-yl) disulphide analogously to Example 33 (a) gave tert-butyl (3RS,4RS)-4-[4-[3-(benzothiazol-2-ylsulphonyl)-propoxy]-phenyl]-3-(1-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless liquid; MS: 671 (M+H)+.

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-87c9535049da46c0a34c01a8d6b05f47
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Linked notes

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