Hydrochloric Acid → HCID 54446458, compound

HRID 1005128

Reaction equation

HRID 1005128 reaction equation
OC1[CH:7]([C:8]2[CH:13]=[CH:12][C:11](O)=[CH:10][CH:9]=2)CCN(C(OC(C)(C)C)=O)C1.ClCCCCOC1CCCCO1.BrCC1C=CC2C(=CC=CC=2)C=1.Cl.[OH:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:58]=[CH:57][C:56]([CH:59]2[CH2:64][CH2:63][N:62]([C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH2:61][CH:60]2[O:72][CH2:73][C:74]2[CH:83]=[CH:82][C:81]3[C:76](=[CH:77][CH:78]=[CH:79][CH:80]=3)[CH:75]=2)=[CH:55][CH:54]=1.C(Br)C1C=CC=CC=1>CO>[CH2:7]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:58]=[CH:57][C:56]([CH:59]2[CH2:64][CH2:63][N:62]([C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH2:61][CH:60]2[O:72][CH2:73][C:74]2[CH:83]=[CH:82][C:81]3[C:76](=[CH:77][CH:78]=[CH:79][CH:80]=3)[CH:75]=2)=[CH:55][CH:54]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 703202-BromomethylnaphthaleneHCID 1704882H-Pyran, 2-(4-chlorobutoxy)tetrahydro-HCID 21713087(3S,4S)-tert-Butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylateHCID 53977546tert-butyl (3RS,4RS)-4-[4-(4-hydroxy-butoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine1-carboxylate

Product 1

HCID 54446458HCID 54446458, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(bbb) In an analogous manner to that described in Example 44 (e), by alkylating tert-butyl (3RS,4RS)-3-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate [Example 46 (b)] with 2-(4-chloro-butoxy)-tetrahydro-2H-pyran there was obtained a mixture of tert-butyl (3RS,4RS)- and (3SR,4SR)-3-hydroxy-4-[4-[4-[(RS)-tetrahydropyran-2-yloxy]-butoxy]-phenyl]-piperidine-1-carboxylate, alkylation of which with 2-bromomethyl-naphthalene analogously to Example 1 (g) gave a mixture of (3RS,4RS)- and (3SR,4SR)-3-(naphthalen-2-ylmethoxy)-4-[4-[4-[(RS)-tetrahydro-pyran-2-yloxy]-butoxy]-phenyl]-piperidine-1-carboxylate. Cleavage of the THP group with hydrogen chloride in methanol analogously to Example 53 (c) yielded tert-butyl (3RS,4RS)-4-[4-(4-hydroxy-butoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine1-carboxylate, alkylation of which with benzyl bromide analogously to Example 1 (g) gave tert-butyl (3RS,4RS)-4-[4-(4-benzyloxy-butoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless oil; MS: 613 (M+NH4)+.

Workup

  1. customthere was obtained
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Sources & evidence

ORD record
ord-d1e5d9b4dc9f4de484a3d1992a1a2682
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Linked notes

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